I used to wear Converse (high and low tops) into the ground when I was in college; I seem to remember them as that not-so-clean sneaker that I slipped my bare (and perhaps black-souled) feet into. Nowadays I think of them as kid sneakers. On a recent trip to London, however, I admired several moms who were rocking the Converse with jeans and a blazer look. Just the right balance of comfort and cool, they make you feel hip—without making it look like you are trying too hard.
When you do get rid of your sneakers, consider sending them to Shoes 4 Africa.